Due Diligence | Podcast on RSS.com

Due Diligence

by Henrick Johansson

Entrepreneurship Investing

Season 1

Microsoft Engineer Turned Stand-Up Comedian - Austin Nasso | Due Diligence Ep. 9

Austin Nasso worked at Microsoft, studied computer science at UCLA, and then decided to become a stand-up comedian. In this episode, Austin talks about leaving Microsoft, getting into comedy, and performing political impressions on tour. He also shows off his impressions of Donald Trump, George W. Bush, and Barack Obama, while Henrick quickly gets roasted. Henrick asks Austin on his background in tech and comedy. See what happens when a stand-up comedian is given a venture capitalist as a target. Austin explains: ■ Why Austin left Microsoft after four years ■ How studying computer science at UCLA shaped his career ■ Why his friends pushed him into stand-up comedy ■ How he developed his political impressions ■ What it's like performing impressions of presidents ■ Why he went on tour as a stand-up comedian ■ The story behind one of his shows and a very familiar audience member ■ Why Henrick is also, somehow, “succulent” ■ What happens when Henrick becomes the subject of the comedy —— About Comp AI Comp AI helps companies build real compliance programs for SOC 2, ISO 27001, GDPR, HIPAA, and more using AI-driven automation. We focus on continuous compliance, audit readiness, and defensible infrastructure, without spreadsheets, chaos, or manual work.

The Million-Dollar Tax Rule Most Founders Miss - Ankur Nagpal (USVC)

Ankur Nagpal is the founder of Teachable, the online education platform acquired in 2020, and the founder behind several companies focused on expanding access to entrepreneurship, financial education, and private market investing. In this episode, Ankur explains how building Facebook apps in college led him into entrepreneurship, why he created Teachable to help creators own their audiences, and what he learned from selling a company during one of the biggest stock market crashes in financial history. He also shares how discovering little-known sections of the U.S. tax code completely changed his understanding of wealth creation and why many founders unknowingly leave millions of dollars on the table. This conversation covers entrepreneurship, Teachable, startup investing, venture capital, private markets, accredited investor laws, tax code strategy, QSBS, Silicon Valley, financial education, founders, AI startups, compliance, and why access—not ability—may be the biggest barrier to building wealth.

Why Open Source AI Beats Big Tech - Thomas Wolf (Hugging Face)

Thomas Wolf is the Co-Founder and Chief Science Officer of Hugging Face, one of the most important companies in open-source AI. Hugging Face has become the central platform for AI builders, researchers, and companies working with machine learning models, datasets, and open-source tools. In this episode, Thomas explains how Hugging Face started as a game company, why the team pivoted into open-source AI, and how a weekend project around Google’s BERT model became one of the first major signals that Hugging Face could become much bigger. He also shares why open-source AI matters, how Hugging Face thinks about robotics, and why the future of AI may depend on openness, affordability, privacy, and giving builders access to powerful tools. Thomas is a physicist, lawyer, PhD, and AI founder. Before building Hugging Face, he studied physics, law, and the rules that govern both the physical world and society. Today, he works at the center of the AI ecosystem, helping make machine learning models, tools, and infrastructure more accessible to developers around the world.

AI Agents Are Coming for Your Job - Flo Crivello (Lindy)

Flo Crivello is the founder and CEO of Lindy, an AI executive assistant company building agents that can manage email, scheduling, research, workflows, and other work that busy professionals do every day. In this episode, Flo explains how Lindy works, why every AI agent gets its own cloud computer, and why AI assistants may soon handle huge parts of the modern knowledge worker’s day. He also shares how Lindy now does 90%+ of what his own executive assistant used to do, how AI will change employment, and why he believes the speed and breadth of this technological shift will be unlike anything we have seen before. Flo is the founder and CEO of Lindy. Lindy builds AI agents for executives, founders, and teams who want to reclaim time from inboxes, calendars, meetings, research, and repetitive workflows. The product connects to email, calendar, messaging, and thousands of integrations so users can delegate tasks to an AI assistant that works across their tools.

Why This VC Writes $150K Checks Based on Vibes - Hubert Thieblot

Hubert Thieblot has spent decades building and investing at the edge of gaming, startups, AI, and Silicon Valley. He is best known as the founder of Curse, the modding platform behind some of the largest communities in games like World of Warcraft and Minecraft. In this episode, Hubert explains why he left Europe for San Francisco, why Silicon Valley rewards speed in a way Europe often does not, and why he believes the best founders are usually ambitious, technical, and willing to move before everything is figured out. He also shares why he sometimes invests based on “vibe,” what he looks for in very young founders, and why he is willing to back 17- and 18-year-olds building robots, machine learning projects, and hard technology.

Why Joining Facebook Was The Worst Decision Ever - Simon Corry (Ramp)

Henrick Johansson sits down with product design leader Simon Corry in New York City for a wide-ranging conversation about creativity, compliance, velocity, and what it really takes to build products people trust. Simon traces his unlikely path from British art school and Royal Mail to Amsterdam’s creative scene, where the early ideas behind WeTransfer grew out of a very real problem: agencies needed a simple, trustworthy way to send large files without accounts, passwords, or friction. From there, the conversation moves through Facebook, anonymity, AI regulation, and Simon’s current work at Ramp, where speed, recruitment, education, and culture are central to scaling without becoming slow. At the heart of the interview is a tension every modern company faces: how do you move fast without losing responsibility, customer empathy, or trust? Simon argues that great teams win by listening closely, staying willing to be wrong, and avoiding the gatekeepers that slow progress down. This is a conversation about design leadership, startup culture, product velocity, AI, compliance, and the human judgment required to build companies that can move quickly without breaking what matters. Featuring stories from WeTransfer, Facebook, Royal Mail, and Ramp, this episode is for anyone interested in product design, leadership, startups, fintech, compliance, AI, and the future of fast-moving teams.

Prison, Rules, and Life Behind Bars - Martin Shkreli

What happens when you sit down for a simple game of chess… and end up in a deep conversation about prison, rules, and human nature?

Why You Should Stop Sending Data to OpenAI - Sam Hogan

Sam Hogan is the founder and CEO of Inference, an AI infrastructure company building a private, cheaper alternative to frontier models from companies like OpenAI, Anthropic, and Google. Instead of forcing companies to send sensitive data to third-party model providers, Inference helps businesses train and host large language models with more control, privacy, and flexibility. In this episode, Sam explains why companies may not want to send their data to frontier AI labs, why he believes open and private model infrastructure will matter, and why Inference is trying to make large language models cheaper and easier for enterprises to run. He also talks about raising $11 million, building one of the largest decentralized GPU clusters on Solana, why the company moved away from crowdsourced compute, and what it takes to build trust when selling AI infrastructure to serious customers.

Why Offices Will Never Be the Same Again - Zoltan Szalas

Zoltan Szalas has spent years building at the intersection of product, growth, AI, workspace, and distributed teams. He is the CEO and Co-Founder of Croissant, a company building the system of record for variable workspace - replacing traditional office leases and workspace stipends with controlled, usage-based spend. In this episode, Zoltan explains why the way we work has permanently changed, why companies are moving away from long-term leases, and why the future of work will look more flexible, distributed, and usage-based. He also shares how AI is forcing leaders to rethink hiring, office strategy, and workforce planning in real time. Zoltan is the CEO & Co-Founder of Croissant. He previously served as Vice President of Product Management at Appfire, Head of Product & Growth at Printify, Director of Product Management for Growth, Data & AI at IBM, and has advised founders and portfolio companies on product, growth, and business strategy.

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Henrick Johansson asks the questions nobody else will. Due Diligence is a new podcast featuring sharp, satirical conversations with founders, operators, and investors in tech. One guest a week. All on the record. Subscribe for new episodes and follow the launch of Due Diligence.